KR20170076117A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device including the same. The compound according to the present invention is used for an organic material layer of an organic electroluminescent device, preferably a light emitting layer or a light emitting auxiliary layer, The driving voltage, the life, and the like can be improved.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, Tang The organic light emitting device having a laminated structure in which the hole layer and the functional layer of the light emitting layer are divided. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials to realize better natural colors. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP and Alq ₃ are widely known as electron transporting layer materials and anthracene derivatives as light emitting layer materials. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.

However, conventional organic material layers are advantageous from the viewpoint of light emitting properties, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of the organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

The present invention has been made to solve the above problems and it is an object of the present invention to provide a novel compound capable of improving the efficiency, lifetime and stability of the organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

At least _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula To form a condensed ring;

R ₁ to R ₈ which do not form a condensed ring with the ring represented by the following formula 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms , A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group , C group ₆ to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphine group, C ₆ to mono- or diaryl phosphine of C ₆₀ blood group and a C ₆ and selected from the group consisting of an aryl amine of the C ₆₀ in or adjacent To form a condensed ring;

Alkyl group of the R ₁ to R _8, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they may be the same or different from each other;

(2)

In Formula 2,

The dotted line means the part where the condensation is made;

Y ₁ to Y ₁₂ are each independently N or C (R ₉ );

R ₉ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ combines mono or diaryl phosphine blood group and a C ₆ ~ tile to selected or adjacent from the group consisting of an aryl amine of the C ₆₀ to which they are attached may form a fused ring of, when the R ₉ multiple individual which Are the same or different from each other;

Alkyl group of the R _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different.

The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .

"Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.

As used herein, the term "alkenyl" is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

The term "alkynyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, , 2-propynyl, and the like, but are not limited thereto.

"Aryl" in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, Click ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

"Alkylsilyl" in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel compound of the present invention is a structure in which dibenzo [b, e] [1,4] dioxin is condensed with a spirofluorene moiety to form a basic skeleton and various substituents are bonded or condensed to the basic skeleton. Characterized in that it is represented by the formula (1)

[Chemical Formula 1]

In Formula 1,

At least _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula To form a condensed ring;

R ₁ to R ₈ which do not form a condensed ring with the ring represented by the following formula 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms , A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group , C group ₆ to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphine group, C ₆ to mono- or diaryl phosphine of C ₆₀ blood group and a C ₆ and selected from the group consisting of an aryl amine of the C ₆₀ in or adjacent (For example, any one of other adjacent R ₁ to R ₈ substituents, etc.) to form a condensed ring;

Alkyl group of the R ₁ to R _8, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they may be the same or different from each other;

(2)

In Formula 2,

The dotted line means the part where the condensation is made;

Y ₁ to Y ₁₂ are each independently N or C (R ₉ );

R ₉ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , in combination with a C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ group selecting or adjacent from the group consisting of an aryl amine of the C ₆₀ (for example, another R ₉ adjacent to exist, and so on) of a condensed ring And when there are a plurality of R < ₉ > s, they are the same as or different from each other;

Alkyl group of the R _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different.

In general, the phosphorescent light emitting layer among the organic material layers included in the organic electroluminescent device includes a host and a dopant to increase the color purity and increase the luminous efficiency. At this time, the host should have a triplet energy gap higher than the dopant. That is, the energy of the lowest excitation state of the host must be higher than the energy of the lowest emission state of the dopant in order to effectively provide phosphorescence from the dopant. In the present invention, the dibenzo [b, e] [1,4] dioxane moiety has a broad singlet energy level and a high triplet energy level. When a specific substituent is introduced into the spiroplorene moiety or the like condensed with dibenzo [b, e] [1,4] dioxine, when the compound of Formula 1 is applied as a host of the light emitting layer, Lt; / RTI >

In addition, since the compound represented by Formula 1 has high triplet energy as described above, it is possible to prevent the exciton generated in the light emitting layer from diffusing (moving) to the adjacent electron transporting layer or hole transporting layer. Accordingly, an organic layer (hereinafter, referred to as a 'light emission-assisting layer') may be formed between the hole transporting layer and the light emitting layer using the compound of Formula 1 or an organic layer (hereinafter referred to as an 'electron transporting layer') may be formed between the light emitting layer and the electron transporting layer. ), Diffusion of the excitons is prevented by the compound. Thus, unlike the conventional organic electroluminescent devices not including the light-emission-assisting layer or the electron-transporting-assisting layer, the excitons substantially contributing to light emission in the light- The luminous efficiency of the device can be improved.

In addition, the compound represented by the formula (1) can control the HOMO and LUMO energy levels according to the substituent introduced into the basic skeleton, and thus can have a wide band gap and a high carrier transporting property.

In addition, the compounds of the present invention are useful as electron donating groups (EDG) in the basic skeleton due to the high hole-transporting ability of oxygen atoms in dibenzo [b, e] [1,4] Can be easily used as a hole transport layer material. Further, when an electron withdrawing group (EWG) having a high electron absorbing property is bonded to the basic skeleton, the entire molecule has a bipolar characteristic, so that the bonding force between holes and electrons can be enhanced.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by any one of Chemical Formulas 3 to 5, but is not limited thereto:

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 3 to 5,

Y ₁ to Y ₁₂ and R ₁ to R ₈ are as defined in the above formula (1).

According to a preferred embodiment of the present invention, at least one of Y ₁ to Y ₄ is C (R ₉ ), and when there are a plurality of R ₉ , they are the same as or different from each other, and R ₉ is Lt; / RTI >

According to one embodiment, preferred according to the present invention, in the above formula 3 to 5, Y ₁ to Y ₁₂ are all C (R _9), wherein and the plurality of R ₉ is the same as or different from each other, R ₉ is In the above formula (2) As defined.

According to a preferred embodiment of the present invention, the R ₉ is a substituent represented by the following formula (6) in view of luminous efficiency, but is not limited thereto:

[Chemical Formula 6]

In Formula 6,

* Denotes the part where the bond is made;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

R ₁₀ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ group selecting or adjacent from the group consisting of an aryl amine of the C ₆₀ (for example, L ₁ or L _2, or adjacent to exist other R _9, or that R _10, etc.) to form a condensed ring;

Wherein L ₁ and the arylene group and a heteroarylalkyl group in the alkylene group, R ₁₀ of the L _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl amine A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 nuclear heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylene group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group When substituted by one or more substituents selected from the group consisting of a reel or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁₀ is selected from the group consisting of hydrogen, deuterium (D), an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nucleus atoms and an arylamine group of C ₆ to C ₆₀ Can be selected from the group.

The compound represented by the general formula (1) of the present invention is a compound in which various substituents, especially an aryl group and / or a heteroaryl group, are introduced into the basic skeleton, whereby the molecular weight of the compound is significantly increased and the glass transition temperature is improved, (E. G., CBP). ≪ / RTI > The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer.

Thus, the compound represented by the general formula (1) of the present invention can be used as an organic material layer of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transporting / The performance and lifetime characteristics of the organic electroluminescent device can be greatly improved when the organic electroluminescent device is applied to an injection layer material, a light emitting auxiliary layer material, and a life improving layer material. Such an organic electroluminescent device can consequently maximize the performance of a full-color organic luminescent panel.

According to a preferred embodiment of the present invention, L ₁ and L ₂ are each independently a linker represented by any one of the following formulas (7) to (11)

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas (7) to (11)

* Denotes the part where the bond is made;

X ₁ is O, S, N (R ₁₂ ) or C (R ₁₃ ) (R ₁₄ );

X ₂ is N or C (R ₁₅ );

p is an integer from 0 to 4;

R ₁₁ is a group selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, an aryloxy group of a C ₆ ~ C ₆₀ of, C C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphosphine groups, C ₆ and the C ₆₀ mono or diaryl phosphine blood group and a C ₆ to C group of ₆₀ selected from the group consisting of an aryl amine or adjacent (e. g., L ₁ or L _2, or adjacent to exist other of R _9, R ₁₀ Or R < _{11 &} gt ;, etc.) to form a condensed ring. When a plurality of R < ₁₁ > s are present, they may be the same or different;

R ₁₂ to R ₁₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ selected from aryl silyl group the group consisting of C ₆₀ or, or adjacent groups (for example, L ₁ or L _2, or that Other R < ₉ >, R < ₁₀ > or R < ₁₁ > and the like present adjacent to each other) to form a condensed ring;

Alkyl group of said R ₁₁ to R _15, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁₀ is a substituent represented by any one of the following formulas (12) to (14) in view of luminous efficiency, but is not limited thereto:

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

In the above Formulas 12 to 14,

* Denotes the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₁₈ );

T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C (R ₁₉ ) (R ₂₀ ), N (R ₂₁ ), O and S, but not both T ₁ and T ₂ are single bonds;

q and r are each independently an integer of 0 to 4;

R ₁₆ and R ₁₇ is a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ of each independently a heavy hydrogen, a halogen, a cyano group, the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of _{C 6 ~ C 60, C 1} ~ C 40 alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 C ₆ to C ₆₀ arylamino groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of or in combination, or the adjacent group to which they are attached may form a fused ring, wherein R a ₁₆ and R < ₁₇ > each are the same or different from each other;

R ₁₈ to R ₂₁ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ to C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from an aryl silyl group the group consisting of C ₆₀ of, or adjacent groups that bind may form a condensed ring, When there are a plurality of R ₁₈ to R ₂₁ each, they are the same as or different from each other;

Alkyl group of said R ₁₆ to R _21, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, the substituents represented by the general formulas (12) to (14) may be substituents represented by any of the following formulas A-1 to A-24,

In the above Formulas A-1 to A-24,

* Denotes the part where the bond is made;

t is an integer from 0 to 5,

u is an integer from 0 to 4;

v is an integer from 0 to 3;

w is an integer from 0 to 2;

R ₂₂ is heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the nucleus of atoms of A C ₆ to C ₆₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryloxy group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ heteroaryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphosphine groups, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ selected from the group consisting arylsilyl of C _60, or adjacent groups (e.g., any one of L ₁ or L _2, or adjacent to other R ₂₂ or that R ₁₆ to R _21, and the like) to form a condensed ring. When a plurality of R _{22 s} are present, they may be the same or different;

Alkyl group of the R _22, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different,

R ₁₆ to R ₂₁ , p and q are as defined in the above formulas (12) to (14).

According to a preferred embodiment of the present invention, R ₁₀ is a substituent represented by the following general formula (15)

[Chemical Formula 15]

In Formula 15,

* Denotes the part where the bond is made;

R ₂₃ and R ₂₄ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ are bonded to each other to C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of, or adjacent groups (e.g., R ₂₃ and R _24, which in ) To form a condensed ring;

Alkyl group of said R ₂₃ and R _24, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, each of R ₂₃ and R ₂₄ is independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, And C ₆ to C ₆₀ arylamine groups.

According to a preferred embodiment of the present invention, R ₂₃ and R ₂₄ are each independently selected from the group consisting of hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, a fluorenyl group, But is not limited to:

[Chemical Formula 16]

In Formula 16,

* Denotes the part where the bond is made;

L ₃ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₂₅ and R ₂₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ groups of the aryl amine group selected or adjacent from the group consisting of (e. g., L ₃ or another R present in the neighborhood ₂₃ or R ₂₄ or the like, or R ₂₅ and R ₂₆ are bonded to each other) to form a condensed ring;

Alkyl groups of the L ₃ arylene group and a heteroarylene group, R ₂₅ and R _26, the alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl amine A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 nuclear heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylene group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group And a silyl group, and when they are substituted with a plurality of substituents, they may be the same or different from each other.

The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:

 In the present invention, the compound represented by Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960), J. Chem. SOC. 4482 (1955) 2457 (1995)). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic Field  Light emitting element

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used singly or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI > Preferably, the organic compound layer containing the compound represented by Formula 1 may be a light emitting layer or a light emitting auxiliary layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, which may include a compound represented by the above formula (1) as a host material. Thus, when the compound represented by Formula 1 is incorporated as a light emitting layer material of an organic electroluminescent device, preferably a green phosphorescent host, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency and power efficiency), lifetime, luminance and driving voltage, etc., can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked. At this time, an electron transporting auxiliary layer may be further laminated between the light emitting layer and the electron transporting layer, and an electron injection layer may further be laminated on the electron transporting layer. In the present invention, at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron transporting supporting layer, and the electron injecting layer may include the compound represented by Formula 1, May include a compound represented by the above formula (1).

In addition, the structure of the organic electroluminescent device of the present invention may be a structure in which not only an anode, one or more organic compound layers and a cathode are sequentially laminated but also an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic compound layer.

The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the light emitting layer or the light emitting auxiliary layer) To form another organic material layer and an electrode.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[ Preparation Example  1] Compound Inv1  Synthesis of

<Step 1> 2- ( Dibenzo [b, e] [1,4] dioxin Yl) -4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan  synthesis

(100 g, 0.38 mol), bis (pinacolato) diboron (115.8 g, 0.46 mol), Pd (dppf) Cl ₂ (31 g, 0.038 mol) mol) and KOAc (111.9 g, 1.14 mol) were placed in a flask, 1,4-dioxane (2 L) was added thereto, and the mixture was heated and stirred for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (dibenzo [b, e] [1,4] dioxin-2-yl) , And 5-tetramethyl-1,3,2-dioxaborolane (73 g, yield 62%).

<Step 2> methyl  5- Chloro -2-( Dibenzo [b, e] [1,4] dioxin -2 days) Benzoate  synthesis

To a solution of 2- (dibenzo [b, e] [1,4] dioxin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxabor Loran (73g, 0.235mol), methyl 2-bromo-5-chlorobenzoate (70.3g, 0.282mol) and Pd (PPh ₃₎ placed in the flask with ₄ (13.5g, 0.011mol), here a 2M Na ₂ CO ₃ saturated aqueous solution (352 ml) and 1,4-dioxane (2 L) were added and dissolved, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain methyl 5-chloro-2- (dibenzo [b, e] [1,4] dioxin- (75.4 g, yield 91%).

<Step 3> 9- Chloro -11H- Benzo [b] fluoreno [2,3-e] [1,4] dioxin -11-one

The dibenzo [b, e] [1,4] dioxin-2-yl) benzoate (75.4 g, 0.214 mol) obtained in the above Step 2 was placed in THF (1 L) After heating, 350 ml of methanesulfonic acid was added, followed by stirring for 4 hours. The resulting solid was filtered, washed with 600 ml of water and 200 ml of ethanol and dried to obtain 9-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] di Oxo-11-one (53.0 g, yield 78%).

<Step 4> Synthesis of 11 - ([1,1'-biphenyl] -2-yl) -9- Chloro -11H- Benzo [b] fluoreno [2,3-e] [1,4] dioxin -11-ol

To a solution of 2-bromo-1,1'-biphenyl (30 ml, 174.0 mmol) in 500 ml of dry THF, the mixture was cooled to -78 ° C, 2.5M n-BuLi (73.2 ml, 183 mmol) Lt; / RTI &gt; To this reaction solution was added 9-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] dioxin-11-one (53.0 g, 165.4 mmol) obtained in the above Step 3 The temperature was then slowly raised to room temperature and stirred for 3 hours. Aqueous ammonium chloride solution was added to terminate the reaction, distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain 11 - ([1,1'-biphenyl] -2-yl) -9- Fluoreno [2,3-e] [1,4] dioxin-11-ol (62.8 g, yield 80%).

&Lt; Step 5 > Inv1  Synthesis of

Benzo [b] fluoreno [2,3-e] [1,4] di (tert-butoxycarbonylamino) Oxin-11-ol (62.8 g, 132.3 mmol) was dissolved in 400 ml of AcOH and heated. After 0.1 ml of sulfuric acid was added, the mixture was stirred for 1 hour. The resulting solid was filtered, washed with 600 ml of water and 200 ml of ethanol and dried to obtain Compound Inv1 (58.6 g, yield 93%).

[ Preparation Example  2] Compound Of Inv2  synthesis

<Step 1> 2- ( Dibenzo [b, e] [1,4] dioxin Yl) -4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan  synthesis

(100 g, 0.38 mol), bis (pinacolato) diboron (115.8 g, 0.46 mol), Pd (dppf) Cl ₂ (31 g, 0.038 mol) mol) and KOAc (111.9 g, 1.14 mol) were placed in a flask, 1,4-dioxane (2 L) was added thereto, and the mixture was heated and stirred for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (dibenzo [b, e] [1,4] dioxin-2-yl) , And 5-tetramethyl-1,3,2-dioxaborolane (73 g, yield 62%).

<Step 2> methyl  4- Chloro -2-( Dibenzo [b, e] [1,4] dioxin -2 days) Benzoate  synthesis

To a solution of 2- (dibenzo [b, e] [1,4] dioxin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxabor Loran (73g, 0.235mol), methyl 2-bromo-4-chlorobenzoate (70.3g, 0.282mol) and Pd (PPh ₃₎ placed in the flask with ₄ (13.5g, 0.011mol), here a 2M Na ₂ CO ₃ saturated aqueous solution (352 ml) and 1,4-dioxane (2 L) were added and dissolved, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain methyl 4-chloro-2- (dibenzo [b, e] [1,4] dioxin- (75.4 g, yield 91%).

<Step 3> 8- Chloro -11H- Benzo [b] fluoreno [2,3-e] [1,4] dioxin -11-one

The dibenzo [b, e] [1,4] dioxin-2-yl) benzoate (75.4 g, 0.214 mol) obtained in the above Step 2 was placed in THF (1 L) After heating, 350 ml of methanesulfonic acid was added, followed by stirring for 4 hours. The resulting solid was filtered, washed with 600 ml of water and 200 ml of ethanol and dried to obtain the compound 8-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] di Oxo-11-one (53.0 g, yield 78%).

<Step 4> Synthesis of 11 - ([1,1'-biphenyl] -2-yl) -8- Chloro -11H- Benzo [b] fluoreno [2,3-e] [1,4] dioxin -11-ol

To a solution of 2-bromo-1,1'-biphenyl (30 ml, 174.0 mmol) in 500 ml of dry THF, the mixture was cooled to -78 ° C, 2.5M n-BuLi (73.2 ml, 183 mmol) Lt; / RTI &gt; Benzo [b] fluoreno [2,3-e] [1,4] dioxin-11-one (53.0 g, 165.4 mmol) obtained in the above Step 3 was added to the reaction solution The temperature was then slowly raised to room temperature and stirred for 3 hours. Aqueous ammonium chloride solution was added to terminate the reaction, distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 11 - ([1,1'-biphenyl] -2-yl) -8-chloro-11H- Fluoreno [2,3-e] [1,4] dioxin-11-ol (62.8 g, yield 80%).

&Lt; Step 5 > Inv2  Synthesis of

Benzo [b] fluoreno [2,3-e] [1,4] di (tert-butoxycarbonylamino) Oxin-11-ol (62.8 g, 132.3 mmol) was dissolved in 400 ml of AcOH and heated. After 0.1 ml of sulfuric acid was added, the mixture was stirred for 1 hour. After the temperature was lowered to room temperature, the resulting solid was filtered, washed with 600 ml of water and 200 ml of ethanol and dried to obtain Compound Inv2 (58.6 g, yield 93%).

[ Preparation Example  3] Compound Inv3  Synthesis of

<Step 1> 2- ( Dibenzo [b, e] [1,4] dioxin Yl) -4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan  synthesis

(100 g, 0.38 mol), bis (pinacolato) diboron (115.8 g, 0.46 mol), Pd (dppf) Cl ₂ (31 g, 0.038 mol) mol) and KOAc (111.9 g, 1.14 mol) were placed in a flask, 1,4-dioxane (2 L) was added thereto, and the mixture was heated and stirred for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (dibenzo [b, e] [1,4] dioxin-2-yl) , And 5-tetramethyl-1,3,2-dioxaborolane (73 g, yield 62%).

&Lt; Step 2 > 2- (2-bromophenyl) dibenzo [b, e] [1,4] dioxine  synthesis

To a solution of 2- (dibenzo [b, e] [1,4] dioxin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxabor Loran (73g, 0.235mol), 1,2- dibromo-benzene (111g, 0.470mol) and _{Pd (PPh 3) 4 (13.5g} , 0.011mol) were placed in the flask, where the saturated 2M Na ₂ CO ₃ An aqueous solution (352 ml) and 1,4-dioxane (2 L) were added and dissolved, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure and then purified by column chromatography to obtain 72.5 g of the compound 2- (2-bromophenyl) dibenzo [b, e] [1,4] 91%).

<Step 3> 2- Bromo -9- (2- ( Dibenzo [b, e] [1,4] dioxin Yl) phenyl) -9H- Fluorene -9-ol

D] benzo [b, e] [1,4] dioxine (59 g, 0.174 mol) obtained in the above Step 2 was dissolved in 500 ml of anhydrous THF, M n-BuLi (73.2 ml, 183 mmol) was added slowly and then allowed to stir for 1 h. After adding 2-bromo-9H-fluoren-9-one (43.0 g, 0.166 mol) to the reaction solution, the temperature was slowly raised to room temperature and stirred for 3 hours. Aqueous ammonium chloride solution was added to terminate the reaction, distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure and then purified by column chromatography to obtain the compound 2-bromo-9- (2- (dibenzo [b, e] [1,4] dioxin- Yl) phenyl) -9H-fluoren-9-ol (68.7 g, yield 80%).

&Lt; Step 4 > Inv3  Synthesis of

(Dibenzo [b, e] [1,4] dioxin-2-yl) phenyl) -9H-fluoren-9-ol obtained in the above Step 3 g, 132.3 mmol) was added to 400 ml of AcOH, and the mixture was heated. Then, 0.1 ml of sulfuric acid was added, followed by stirring for 1 hour. The resulting solid was filtered, washed with 600 ml of water and 200 ml of ethanol and dried to obtain Compound Inv3 (61.7 g, yield 93%).

[ Synthetic example  One] Cpd  Synthesis of 50

(9.8 g, 9.67 mmol), NaOH (1.06 g, 26.4 mmol), and THF / MeOH (3.5 g, 7.70 mmol) H ₂ O (100 ml / 50 ml) was added and stirred. Then, insert the _{Pd (PPh 3) 4 (5} mol%, 0.51 g) in 40 ℃, and the mixture was stirred at 80 ℃ for 12 hours.

After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain 4.1 g of the compound Cpd 50 (yield: 80%).

HRMS [M] &lt; ⁺ & gt ^; : 663.220

[ Synthetic example  2] Cpd51  Synthesis of

Dibenzo [b, d] furan-4-ylboronic acid was used in place of (9-phenyl-9H-carbazol- Compound Cpd51 was obtained.

HRMS [M] &lt; ⁺ & gt ^; : 588.173

[ Synthetic example  3] Cpd52  Synthesis of

The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] thiophen-4-ylboronic acid was used in place of (9-phenyl-9H-carbazol- To obtain the title compound Cpd52.

HRMS [M] &lt; ⁺ & gt ^; : 604.150

[ Synthetic example  4] Cpd53  Synthesis of

Dibenzo [b, d] furan-2-ylboronic acid was used in place of (9-phenyl-9H-carbazol- To obtain a compound Cpd53.

HRMS [M] &lt; ⁺ & gt ^; : 588.173

[ Synthetic example  5] Cpd54  Synthesis of

The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] thiophen-2-ylboronic acid was used in place of (9-phenyl-9H-carbazol- To obtain the title compound Cpd54.

HRMS [M] &lt; ⁺ & gt ^; : 604.150

[ Synthetic example  6] Cpd  Synthesis of 77

Except that (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd77.

HRMS [M] &lt; ⁺ & gt ^; : 729.242

[ Synthetic example  7] Cpd  Synthesis of 83

(9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazol-3-yl ) Boronic acid as a starting material, the procedure of Synthetic Example 1 was repeated to obtain the title compound Cpd83.

HRMS [M] &lt; ⁺ & gt ^; : 818.268

[ Synthetic example  8] Cpd92  Synthesis of

(9- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -9H-carbazole 3-yl) boronic acid was used in place of 2-chloro-4-fluoro-4-methoxybenzoic acid to obtain the title compound Cpd92.

HRMS [M] &lt; ⁺ & gt ^; : 894.299

[ Synthetic example  9] Cpd  Synthesis of 95

(9- (4 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1 -Biphenyl] -4-yl) -9H-carbazol-3-yl) boronic acid was used in place of the compound obtained in Synthesis Example 1 to obtain the title compound Cpd95.

HRMS [M] &lt; ⁺ & gt ^; : 970.331

[ Synthetic example  10] Cpd  Synthesis of 96

(9- (3 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1 -Biphenyl] -4-yl) -9H-carbazol-3-yl) boronic acid was used in place of the compound obtained in Synthesis Example 1 to obtain the title compound Cpd96.

HRMS [M] &lt; ⁺ & gt ^; : 970.331

[ Synthetic example  11] Cpd  Synthesis of 97

(9- (4 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1 -Biphenyl] -3-yl) -9H-carbazol-3-yl) boronic acid was used as the starting material to obtain the title compound Cpd97.

HRMS [M] &lt; ⁺ & gt ^; : 970.331

[ Synthetic example  12] Cpd  98 Synthesis

(9- (3 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1 -Biphenyl] -3-yl) -9H-carbazol-3-yl) boronic acid was used as the starting material to obtain the title compound Cpd98.

HRMS [M] &lt; ⁺ & gt ^; : 970.331

[ Synthetic example  13] Cpd  148 Synthesis

Except that (4- (naphthalen-1-yl (phenyl) amino) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol- To give the title compound Cpd148.

HRMS [M] &lt; ⁺ & gt ^; : 715.251

[ Synthetic example  14] Cpd  Synthesis of 149

Except that (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd149.

HRMS [M] &lt; ⁺ & gt ^; : 817.298

[ Synthetic example  15] Cpd  Synthesis of 152

(9,9-dimethyl-9H-fluoren-2-yl) boronic acid in place of (9- Amino) phenyl) boronic acid was used in place of the compound obtained in Synthesis Example 1, the title compound Cpd152 was obtained.

HRMS [M] &lt; ⁺ & gt ^; : 857.329

[ Synthetic example  16] Cpd  Synthesis of 154

Except that (4- (naphthalen-1-yl (phenyl) amino) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol- To give the title compound Cpd154.

HRMS [M] &lt; ⁺ & gt ^; : 715.251

[ Synthetic example  17] Cpd  Synthesis of 155

Except that (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd155.

HRMS [M] &lt; ⁺ & gt ^; : 817.298

[ Synthetic example  18] Cpd  158 Synthesis

(9,9-dimethyl-9H-fluoren-2-yl) boronic acid in place of (9- Amino) phenyl) boronic acid, the title compound Cpd158 was obtained.

HRMS [M] &lt; ⁺ & gt ^; : 857.329

[ Synthetic example  19] Cpd  Synthesis of 179

Except that (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd179.

HRMS [M] &lt; ⁺ & gt ^; : 817.298

[ Synthetic example  20] Of Cpd150  synthesis

4-yl) amine (3.8 g, 12.0 mmol) was dissolved in 100 ml of toluene and then Pd ₂ (dba) ₃ (0.9 g, , 1.0 mmol) were added under nitrogen. Then, NaOtBu (2.9 g, 30 mmol) was added, and (t-Bu) ₃ P (1.0 mL, 1.0 mmol) was added to the reaction solution and the mixture was refluxed with stirring for 5 hours.

After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain Compound Cpd 150 (6.4 g, yield 86%).

HRMS [M] &lt; ⁺ & gt ^; : 741.267

[ Synthetic example  21] Cpd  156 Synthesis

The same procedure as in Synthesis Example 20 was conducted except that Inv2 was used instead of Inv1 to obtain the title compound Cpd156.

HRMS [M] &lt; ⁺ & gt ^; : 741.267

[ Synthetic example  22] Cpd  180 Synthesis

The same procedure as in Synthesis Example 20 was conducted except that Inv3 was used instead of Inv1 to obtain the title compound Cpd180.

HRMS [M] &lt; ⁺ & gt ^; : 741.267

[ Example  1] Green organic Field  Fabrication of light emitting device

Compound Cpd 148 synthesized in Synthesis Example 13 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was produced as follows.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / compound cpd148 (40 nm) / CBP + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order to obtain a green organic electroluminescent device.

Here, the structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP used are as follows.

[ Example  2 ~ 10] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound shown in the following Table 1 was used in place of the compound Cpd148 used in Example 1, respectively.

[ Comparative Example  1] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound Cpd148 used in Example 1 was not used.

[ Evaluation example  One]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic electroluminescent device manufactured in each of Examples 1 to 10 and Comparative Example 1, and the results are shown in Table 1 .

Sample Light-emitting auxiliary layer material The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 Cpd148 6.75 518 41.8 Example 2 Cpd149 6.80 517 41.5 Example 3 Cpd150 6.77 518 42.0 Example 4 Cpd152 6.72 520 41.9 Example 5 Cpd154 6.80 518 41.5 Example 6 Cpd155 6.69 520 41.8 Example 7 Cpd156 6.82 517 41.8 Example 8 Cpd158 6.75 518 41.8 Example 9 Cpd179 6.80 520 42.0 Example 10 Cpd180 6.77 518 42.0 Comparative Example 1 - 6.93 516 38.2

As shown in Table 1, the green organic electroluminescent devices of Examples 1 to 10 using the compounds represented by the formula (1) (compounds Cpd148 to Cpd180) according to the present invention as light emitting auxiliary layer materials, The driving voltage was slightly lower than that of the green organic electroluminescent device of Comparative Example 1 used as the light emitting layer material and the current efficiency was superior to that of the green organic electroluminescent device of Comparative Example 1. [

[ Example  11] Red organic Field  Fabrication of light emitting device

Compound Cpd 148 synthesized in Synthesis Example 13 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was prepared as follows.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was cleaned, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a UV OZONE cleaner (Powersonic 405, Hwasin Tech). Then, the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / compound cpd148 (40 nm) / CBP + 10% (piq) ₂ Ir (acac) (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce a red organic electroluminescent device.

The structures of m-MTDATA, TCTA, CBP and BCP used herein are as described in Example 1, and (piq) ₂ Ir (acac) is as follows.

[ Example  12 ~ 20] Red organic Field  Fabrication of light emitting device

A red organic electroluminescent device was manufactured in the same manner as in Example 11, except that the compound shown in the following Table 2 was used in place of the compound Cpd 148 used in Example 11.

[ Comparative Example  2] Red organic Field  Fabrication of light emitting device

A red organic electroluminescent device was produced in the same manner as in Example 11, except that the compound Cpd 148 used in Example 11 was not used.

[ Evaluation example  2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each red organic electroluminescent device fabricated in Examples 11 to 20 and Comparative Example 2. The results are shown in Table 2 below.

Sample Light-emitting auxiliary layer material The driving voltage (V) Current efficiency (cd / A) Example 11 Cpd148 5.13 11.1 Example 12 Cpd149 5.16 11.5 Example 13 Cpd150 5.17 11.6 Example 14 Cpd152 5.14 11.0 Example 15 Cpd154 5.15 10.8 Example 16 Cpd155 5.10 11.2 Example 17 Cpd156 5.15 11.0 Example 18 Cpd158 5.20 11.3 Example 19 Cpd179 5.15 11.0 Example 20 Cpd180 5.10 11.3 Comparative Example 2 - 5.25 8.2

As shown in Table 2, the red organic electroluminescent devices of Examples 11 to 20, in which the compounds represented by Formula 1 (compounds Cpd148 to Cpd180) according to the present invention were used as the light emitting auxiliary layer material, As compared with the red organic electroluminescent device of Comparative Example 2 used as the light emitting layer material, it was found that the driving voltage was slightly lower and the current efficiency was better.

[ Example  21] Blue organic Field  Fabrication of light emitting device

The compound Cpd 148 synthesized in Synthesis Example 13 was subjected to high purity sublimation purification by a conventionally known method, and a blue organic electroluminescent device was prepared as follows.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Powersonic 405, Hoshin Tec), the substrate was cleaned using UV for 5 minutes, The substrate was transferred to an evaporator.

On the ITO transparent electrode thus prepared, a mixture of DS-205 (80 nm) / NPB (15 nm) / compound Cpd 148 (15 nm) / ADN + 5% DS-405 (Doosan) ) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce a blue organic electroluminescent device.

The BCP used is as described in Example 1, and the structures of NPB and ADN are as follows.

[ Example  22 ~ 30] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 21 except that the compound described in Table 3 was used instead of the compound Cpd 148 used in Example 21.

[ Comparative Example  3] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 21 except that the compound Cpd 148 used in Example 21 was not used.

[ Evaluation example  3]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices manufactured in Examples 21 to 30 and Comparative Example 3, and the results are shown in Table 3 below.

Sample Light-emitting auxiliary layer material The driving voltage (V) Current efficiency (cd / A) Example 21 Cpd148 5.50 6.9 Example 22 Cpd149 5.60 6.6 Example 23 Cpd150 5.55 6.8 Example 24 Cpd152 5.60 6.9 Example 25 Cpd154 5.51 6.6 Example 26 Cpd155 5.55 6.8 Example 27 Cpd156 5.51 6.0 Example 28 Cpd158 5.55 6.4 Example 29 Cpd179 5.60 6.5 Example 30 Cpd180 5.65 6.8 Comparative Example 3 - 5.60 4.8

As shown in Table 3, the red organic electroluminescent devices of Examples 21 to 30, in which the compounds represented by Formula 1 (compounds Cpd148 to Cpd180) according to the present invention were used as the light emitting auxiliary layer material, The driving voltage was similar to that of the blue organic electroluminescent device of Comparative Example 3, which was used as a light emitting layer material, but the current efficiency was superior to that of the organic electroluminescent device of Comparative Example 3.

[ Example  31] Green organic Field  Fabrication of light emitting device

The compound Cpd50 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / compound Cpd50 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF 1 nm) / Al (200 nm) in this order.

[ Example  32 ~ 42] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 31 except that the compound shown in the following Table 4 was used in place of the compound Cpd50 used in Example 31, respectively.

[ Comparative Example  4] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 31 except that CBP was used in place of the compound Cpd50 used as a light emitting host material in forming the light emitting layer in Example 31. [

[ Evaluation example  4]

The driving voltage, the current efficiency and the emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices fabricated in Examples 31 to 42 and Comparative Example 4. The results are shown in Table 4 .

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 31 Cpd50 6.79 517 40.8 Example 32 Cpd51 6.81 518 41.1 Example 33 Cpd52 6.79 517 40.8 Example 34 Cpd53 6.78 515 42.4 Example 35 Cpd54 6.81 518 41.1 Example 36 Cpd77 6.79 517 40.8 Example 37 Cpd83 6.81 518 41.1 Example 38 Cpd92 6.79 517 40.8 Example 39 Cpd95 6.79 517 40.8 Example 40 Cpd96 6.81 518 41.1 Example 41 Cpd97 6.79 517 40.8 Example 42 Cpd98 6.79 517 40.8 Comparative Example 4 CBP 6.93 516 38.2

As shown in Table 4, in the case of the green organic electroluminescent devices of Examples 31 to 42 using the synthesized compounds (compounds Cpd50 to Cpd98) as the light emitting layer materials, the green organic electroluminescent device of Comparative Example 4 using conventional CBP Which is superior in current efficiency and driving voltage.

[ Example  43] blue organic Field  Fabrication of light emitting device

The compound Cpd50 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and a blue organic electroluminescent device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

The ITO transparent electrode thus prepared was laminated in the order of CuPc (10 nm) / TPAC (30 nm) / compound Cpd50 + 7% Flrpic (30 nm) / Alq ₃ (30 nm) / LiF (0.2 nm) / Al Thereby preparing an organic electroluminescent device.

The structures of CuPc, TPAC and Flrpic used herein are as follows.

[ Example  44 ~ 47] Blue organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 43 except that the compound shown in the following Table 5 was used in place of the compound Cpd50 used in Example 1, respectively.

[ Comparative Example  5] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 43 except that CBP was used in place of the compound Cpd50 used as a light emitting host material in the light emitting layer formation in Example 43.

[ Evaluation example  5]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices fabricated in Examples 43 to 47 and Comparative Example 5, and the results are shown in Table 5 .

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 43 Cpd50 7.29 473 6.90 Example 44 Cpd51 7.30 474 6.34 Example 45 Cpd52 7.24 475 6.55 Example 46 Cpd53 7.15 471 6.94 Example 47 Cpd54 7.23 472 6.25 Comparative Example 5 CBP 7.80 474 5.80

As shown in Table 5, the blue organic electroluminescent devices of Examples 43 to 47 using the compounds (Cpd50 to Cpd54) according to the present invention as light emitting layer materials were the blue organic electroluminescent devices of Comparative Example 5 using CBP Which is superior in current efficiency and driving voltage.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

Claims (13)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
At least _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula To form a condensed ring;
R ₁ to R ₈ which do not form a condensed ring with the ring represented by the following formula 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms , A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group , C group ₆ to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphine group, C ₆ to mono- or diaryl phosphine of C ₆₀ blood group and a C ₆ and selected from the group consisting of an aryl amine of the C ₆₀ in or adjacent To form a condensed ring;
Alkyl group of the R ₁ to R _8, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they may be the same or different from each other;
(2)

In Formula 2,
The dotted line means the part where the condensation is made;
Y ₁ to Y ₁₂ are each independently N or C (R ₉ );
R ₉ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ combines mono or diaryl phosphine blood group and a C ₆ ~ tile to selected or adjacent from the group consisting of an aryl amine of the C ₆₀ to which they are attached may form a fused ring of, when the R ₉ multiple individual which Are the same or different from each other;
Alkyl group of the R _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different. The method according to claim 1,
Wherein the compound represented by Formula 1 is a compound represented by any one of Chemical Formulas 3 to 5:
(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 3 to 5,
Y ₁ to Y ₁₂ and R ₁ to R ₈ are as defined in claim 1, respectively. The method according to claim 1,
Wherein R ₉ is a substituent represented by the following formula (6):
[Chemical Formula 6]

In Formula 6,
* Denotes the part where the bond is made;
L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
R ₁₀ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ by groups bonded to adjacent or selected from the group consisting of an aryl amine of the C ₆₀ can form a condensed ring;
Wherein L ₁ and the arylene group and a heteroarylalkyl group in the alkylene group, R ₁₀ of the L _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl amine A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 nuclear heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylene group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group When substituted by one or more substituents selected from the group consisting of a reel or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other. The method of claim 3,
Wherein L &lt; _{1 &gt;} and L &lt; ₂ &gt; are each independently a linker represented by any one of the following formulas (7)
(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas (7) to (11)
* Denotes the part where the bond is made;
X ₁ is O, S, N (R ₁₂ ) or C (R ₁₃ ) (R ₁₄ );
X ₂ is N or C (R ₁₅ );
p is an integer from 0 to 4;
R ₁₁ is a group selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, an aryloxy group of a C ₆ ~ C ₆₀ of, C C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphosphine groups, C ₆ to mono- or diaryl phosphine of C ₆₀ blood group and a C ₆ to C to ₆₀ selected from the group consisting of an aryl amine or bonded adjacent group to form a condensed ring, and when the R ₁₁ multiple individuals they are equal to each other Or different;
R ₁₂ to R ₁₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ of arylsilyl, by combining groups of adjacent, may form a condensed ring;
Alkyl group of said R ₁₁ to R _15, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other. The method of claim 3,
Wherein R ₁₀ is hydrogen, deuterium _{(D), C 6 ~ C} 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ compound selected from the group consisting of an aryl amine of the C ₆₀ in. The method of claim 3,
Wherein R &lt; ₁₀ &gt; is a substituent represented by any one of the following general formulas (12) to (14)
[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

In the above Formulas 12 to 14,
* Denotes the part where the bond is made;
Z ₁ to Z ₅ are each independently N or C (R ₁₈ );
T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C (R ₁₉ ) (R ₂₀ ), N (R ₂₁ ), O and S, but not both T ₁ and T ₂ are single bonds;
q and r are each independently an integer of 0 to 4;
R ₁₆ and R ₁₇ is a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ of each independently a heavy hydrogen, a halogen, a cyano group, the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of _{C 6 ~ C 60, C 1} ~ C 40 alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 C ₆ to C ₆₀ arylamino groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of or in combination, or the adjacent group to which they are attached may form a fused ring, wherein R a ₁₆ and R &lt; ₁₇ &gt; each are the same or different from each other;
R ₁₈ to R ₂₁ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ to C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from an aryl silyl group the group consisting of C ₆₀ of, or adjacent groups that bind may form a condensed ring, When there are a plurality of R ₁₈ to R ₂₁ each, they are the same as or different from each other;
Alkyl group of said R ₁₆ to R _21, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other. The method of claim 3,
Wherein R &lt; ₁₀ &gt; is a substituent represented by any of the following formulas A-1 to A-24:

In the above Formulas A-1 to A-24,
* Denotes the part where the bond is made;
t is an integer from 0 to 5,
u is an integer from 0 to 4;
v is an integer from 0 to 3;
w is an integer from 0 to 2;
q and r are each independently an integer of 0 to 4;
R _16, R ₁₇ and R ₂₂ is a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl groups, C ₆ each independently represent a deuterium, a halogen, a cyano group, ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C of ₆ ~ C ₆₀ aryl amine group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ selected from the group consisting arylsilyl of C ₆₀ of, or by groups coupled to or adjacent to which they are attached may form a condensed ring , When R ₁₆ , R ₁₇ and R ₂₂ are plural, they are the same as or different from each other;
R ₁₈ to R ₂₁ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of, or combine tile adjacent to form a condensed ring;
Alkyl group of said R ₁₆ to R _22, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other. The method of claim 3,
Wherein R ₁₀ is a substituent represented by the following formula (15):
[Chemical Formula 15]

In Formula 15,
* Denotes the part where the bond is made;
R ₂₃ and R ₂₄ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of, or combine tile adjacent to form a condensed ring;
Alkyl group of said R ₂₃ and R _24, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they may be the same or different from each other. 9. The method of claim 8,
Each of R ₂₃ and R ₂₄ is independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine group &Lt; / RTI &gt; 9. The method of claim 8,
Each of R ₂₃ and R ₂₄ is independently selected from the group consisting of hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, a fluorenyl group, and a substituent group represented by the following Formula 16;
[Chemical Formula 16]

In Formula 16,
* Denotes the part where the bond is made;
L ₃ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R ₂₅ and R ₂₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ by groups bonded to adjacent or selected from the group consisting of an aryl amine of the C ₆₀ can form a condensed ring;
Alkyl groups of the L ₃ arylene group and a heteroarylene group, R ₂₅ and R _26, the alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl amine A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 nuclear heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylene group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group And a silyl group, and when they are substituted with a plurality of substituents, they may be the same or different from each other. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound represented by the general formula (1). 13. The method of claim 12,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron transporting auxiliary layer, an electron injecting layer, a lifetime improving layer, a light emitting layer and a light emitting auxiliary layer.